By Dave Quinn / People
July 6, 2017

In 2015, Madonna made headlines when she admitted she had dated rapper Tupac Shakur years before his death. Now, an uncovered letter from the late star to the pop icon reveals that race was a big factor in their breakup.

On Wednesday, TMZ published portions of a previously unseen letter Tupac penned while at the Clinton Correctional Facility, where he was serving time on sexual abuse charges.

Tupac is incredibly candid in the note — dated Jan. 15, 1995, 4:30 a.m. and addressed simply to “M’ — often expressing his sorrow for their breakup and admitting he waited a long time to write the note because he was “struggling to find all the answers” so that he “wouldn’t leave any unanswered questions.”

“For you to be seen with a black man wouldn’t in any way jeopardize your career, if anything it would make you seem that much more open and exciting,” Tupac wrote. “But for me at least in my previous perception I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was.”

(L-R) Raquel Welch, Madonna and Tupac Shakur at the Interview Magazine party, March 1, 1994 in New York.
Patrick McMullan—Getty Images

“I never meant to hurt you,” he added.

There are multiple apologies to Madonna throughout the letter and admissions of mistakes Tupac claimed he made. “I must apologize to you because like you said I haven’t been the kind of friend I know I am capable of being,” he said.

He explained he was angry after an interview Madonna gave in which she allegedly said, “‘I’m off to rehabilitate all the rappers & basketball players.’ ”

Read More: 20 Years After Tupac’s Death: ‘A Symbol of Possibility, of Life Cut Short’

“Those words cut me deep seeing how I had never known you to be with any rappers besides myself,” Tupac wrote. “It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things. …Can you feel me?”

“In the time since, as you can see, I have grown both spiritually and mentally,” Tupac continued. “It no longer matters how I’m perceived. Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.”

Towards the end of the letter, Tupac asked for Madonna’s friendship and gave her some advice — though both items came with an impending sense of doom for the rapper, who would die from wounds inflicted in a drive-by shooting a little over a year later.

“I offer my friendship once again, this time stronger and focused. If you are still interested I would like to further discuss this with you but some of it couldn’t wait. I felt compelled to tell you…just in case anything happened to me,” he said. “Please be careful Madonna. Everyone is not as honorable as they seem there are those whose hearts bleed with envy & evil. They would not hesitate to do you harm!” Tupac wrote. “Let my 6 bullets be proof of that!”

After signing the letter “Always 2Pac Tupac Shakur,” he added a final request.

Read More: Biggie Smalls and Tupac

“I don’t know how you feel about visiting me but if you could find it in your heart I would love to speak face to face with you,” he said. “It’s funny but this experience has taught me to not take time 4 granted.”

Four sections from Tupac’s letter were redacted by TMZ. Gotta Have Rock and Roll will auction off the full document between July 19-28, with a starting bid of $100,000.

This article originally appeared on PEOPLE.com.

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